Trifluoroacetic acid → HCID 21515344, compound

HRID 1284007Notes

Reaction equation

HRID 1284007 reaction equation
[CH3:1][O:2][C:3]([O:5][CH:6]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]([O:9]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:8])=[S:4].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[CH3:1][O:2][C:3]([O:5][CH:6]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:7]([OH:9])=[O:8])=[S:4]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86733870HCID 86733870, compound

Product 1

HCID 21515344HCID 21515344, compound

Reagents, catalysts & solvents 1

HCID 7519AnisoleCatalyst

Procedure

3.92 g. (10 mM) of the benzhydryl ester from Example 2 are stirred together with 30 ml. of trifluoroacetic acid and a few drops of anisole at 0° for 10 minutes. After distilling the solvent off in vacuum, the residue is treated with petroleum ether until it becomes solid. The solid is then stirred for five minutes in 50 ml. of sodium bicarbonate and filtered. After acidification with 2 N hydrochloric acid and extraction twice, each time with 20 ml. of ether and then drying from the organic phase, 1.2 g. of α-[(methoxycarbonothioyl)oxy]benzeneacetic acid are obtained from the filtrate in the form of white crystals after crystallization from cyclohexane/benzol, m.p. 86°-87°.

Workup

  1. distillationAfter distilling the solvent off in vacuum
  2. additionthe residue is treated with petroleum ether until it
  3. filtrationof sodium bicarbonate and filtered
  4. extractionAfter acidification with 2 N hydrochloric acid and extraction twice
  5. dry with materialof ether and then drying from the organic phase, 1.2 g

Sources & evidence

ORD record
ord-25f2753acb7a465e83c2672fb985721d
Source dataset
uspto-grants-1976_08
Patent number
US03978050

Reaction notes

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